N^α-benzyloxycarbonyl-D-hemilanthionyl-L-isoleucyl-O-diphenylphosphoryl-L-seryl-L-leucine methyl ester N^α'-trityl-L-hemilanthionine α'-methyl ester

Base Information

• Chemical Name: N^α-benzyloxycarbonyl-D-hemilanthionyl-L-isoleucyl-O-diphenylphosphoryl-L-seryl-L-leucine methyl ester N^α'-trityl-L-hemilanthionine α'-methyl ester
• CAS No.: 75832-11-0
• Molecular Formula: C₆₂H₇₂N₅O₁₃PS
• Molecular Weight: 1158.32

Synonyms:N^α-benzyloxycarbonyl-D-hemilanthionyl-L-isoleucyl-O-diphenylphosphoryl-L-seryl-L-leucine methyl ester N^α'-trityl-L-hemilanthionine α'-methyl ester

Chemical Property of N^α-benzyloxycarbonyl-D-hemilanthionyl-L-isoleucyl-O-diphenylphosphoryl-L-seryl-L-leucine methyl ester N^α'-trityl-L-hemilanthionine α'-methyl ester

Chemical Property:

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Technology Process of N^α-benzyloxycarbonyl-D-hemilanthionyl-L-isoleucyl-O-diphenylphosphoryl-L-seryl-L-leucine methyl ester N^α'-trityl-L-hemilanthionine α'-methyl ester

There total 6 articles about N^α-benzyloxycarbonyl-D-hemilanthionyl-L-isoleucyl-O-diphenylphosphoryl-L-seryl-L-leucine methyl ester N^α'-trityl-L-hemilanthionine α'-methyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 83.0%

(S)-2-[(S)-2-((2S,3S)-2-{(S)-2-Benzyloxycarbonylamino-3-[(R)-2-methoxycarbonyl-2-(trityl-amino)-ethylsulfanyl]-propionylamino}-3-methyl-pentanoylamino)-3-hydroxy-propionylamino]-4-methyl-pentanoic acid methyl ester (75816-53-4) + chlorophosphoric acid diphenyl ester (2524-64-3) → Nα-benzyloxycarbonyl-D-hemilanthionyl-L-isoleucyl-O-diphenylphosphoryl-L-seryl-L-leucine methyl ester Nα'-trityl-L-hemilanthionine α'-methyl ester (75832-11-0)

Guidance literature:

In pyridine; for 1h; Ambient temperature;

Reference yield:

(S)-Leu-OMe (2666-93-5) → Nα-benzyloxycarbonyl-D-hemilanthionyl-L-isoleucyl-O-diphenylphosphoryl-L-seryl-L-leucine methyl ester Nα'-trityl-L-hemilanthionine α'-methyl ester (75832-11-0)

Guidance literature:

Multi-step reaction with 6 steps

2: 1.) hydrogen, 2.) 0.4N-hydrogene chloride in methanol / 1.) 10percent palladium-charcoal / 1.) 1percent acetic acid in methanol, 2.5 h, 2.) -15 deg C

3: 80 percent / dicyclohexylcarbodi-imide, N-hydroxysuccinimide / CHCl₃ / 1.) 0 deg C, 30 min, 2.) room temperature, 5 h

4: 93 percent / 2-mercaptoethanol, 7N hydrogen chloride / methanol; diethyl ether

5: 65 percent / triethylamine / dimethylformamide

6: 83 percent / pyridine / 1 h / Ambient temperature

With hydrogenchloride; 1-hydroxy-pyrrolidine-2,5-dione; hydrogen; triethylamine; dicyclohexyl-carbodiimide; 2-hydroxyethanethiol; palladium on activated charcoal; In pyridine; methanol; diethyl ether; chloroform; N,N-dimethyl-formamide;

Reference yield:

Z-Ser-Leu-OMe (17331-94-1) → Nα-benzyloxycarbonyl-D-hemilanthionyl-L-isoleucyl-O-diphenylphosphoryl-L-seryl-L-leucine methyl ester Nα'-trityl-L-hemilanthionine α'-methyl ester (75832-11-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) hydrogen, 2.) 0.4N-hydrogene chloride in methanol / 1.) 10percent palladium-charcoal / 1.) 1percent acetic acid in methanol, 2.5 h, 2.) -15 deg C

2: 80 percent / dicyclohexylcarbodi-imide, N-hydroxysuccinimide / CHCl₃ / 1.) 0 deg C, 30 min, 2.) room temperature, 5 h

3: 93 percent / 2-mercaptoethanol, 7N hydrogen chloride / methanol; diethyl ether

4: 65 percent / triethylamine / dimethylformamide

5: 83 percent / pyridine / 1 h / Ambient temperature

With hydrogenchloride; 1-hydroxy-pyrrolidine-2,5-dione; hydrogen; triethylamine; dicyclohexyl-carbodiimide; 2-hydroxyethanethiol; palladium on activated charcoal; In pyridine; methanol; diethyl ether; chloroform; N,N-dimethyl-formamide;

upstream raw materials:

(S)-2-[(S)-2-((2S,3S)-2-{(S)-2-Benzyloxycarbonylamino-3-[(R)-2-methoxycarbonyl-2-(trityl-amino)-ethylsulfanyl]-propionylamino}-3-methyl-pentanoylamino)-3-hydroxy-propionylamino]-4-methyl-pentanoic acid methyl ester

chlorophosphoric acid diphenyl ester

(S)-Leu-OMe

Z-Ser-Leu-OMe

Downstream raw materials:

N^α-benzyloxycarbonyl-D-hemilanthionyl-L-isoleucyldehydroalanyl-L-leucine L-hemilanthionine α'-methyl ester hydrochloride

N^α-benzyloxycarbonyl-D-hemilanthionyl-L-isoleucyldehydroalanyl-L-leucine N^α'-trityl-L-hemilanthionine α'-methyl ester

N^α-benzyloxycarbonyl-D-hemilanthionyl-L-isoleucyldehydroalanyl-L-leucyl-L-hemilanthionine α'-methyl ester

N^α-benzyloxycarbonyl-D-hemilanthionyl-L-isoleucyldehydroalanyl-L-leucine methyl ester N^α'-trityl-L-hemilanthionine α'-methyl ester

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